Abstract: A lactone compound is represented by general formula (A), and an ether compound is represented by general formula (B). In formula (A), R is a hydrogen atom or R1. When R is a hydrogen atom, R? is R1, the carbon bond (1) is a single bond or a double bond, and the carbon bond (2) is a single bond. When R is R1, R? is a hydrogen atom or R1, both the carbon bonds (1) and (2) are a single bond, or one of them is a double bond and the other is a single bond. In formula (B), R? is R1. R1 represents a specific alkyl group, a specific alkenyl group, a specific alkynyl group, or an aryl group. In formulas (A) and (B), n is 0 or 1.

Abstract: A cooling agent composition contains a 2,2,6-trimethylcyclohexanecarboxylic acid derivative represented by the following general formula (1). The symbol * represents an asymmetric carbon atom. X represents NH, N(ZAr2), O or S, Z represents a single bond or an alkylene group having 1 to 3 carbon atoms which may have a substituent, Ar2 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent. Y each independently represents a methylene group which may have a substituent, and n represents an integer of 0 to 3. Ar1 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent.

Abstract: A cooling agent composition includes a methyl menthol derivative represented by the following general formula (1). In the formula (1), a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent.

Abstract: A lactone compound is represented by general formula (A), and an ether compound is represented by general formula (B). In formula (A), R is a hydrogen atom or R1. When R is a hydrogen atom, R? is R1, the carbon bond (1) is a single bond or a double bond, and the carbon bond (2) is a single bond. When R is R1, R? is a hydrogen atom or R1, both the carbon bonds (1) and (2) are a single bond, or one of them is a double bond and the other is a single bond. In formula (B), R? is R1. R1 represents a specific alkyl group, a specific alkenyl group, a specific alkynyl group, or an aryl group. In formulas (A) and (B), n is 0 or 1.

Abstract: A cooling agent composition contains a 2,2,6-trimethylcyclohexanecarboxylic acid derivative represented by the following general formula (1). The symbol * represents an asymmetric carbon atom. X represents NH, N(ZAr2), O or S, Z represents a single bond or an alkylene group having 1 to 3 carbon atoms which may have a substituent, Ar2 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent. Y each independently represents a methylene group which may have a substituent, and n represents an integer of 0 to 3. Ar1 represents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent.

Abstract: A cooling agent composition includes a methyl menthol derivative represented by the following general formula (1). In the formula (1), a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent.

Abstract: The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation, malodor, bitterness, or the like, it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B).

Abstract: The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation, malodor, bitterness, or the like, it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B).

Abstract: A method for producing an optically active isopulegol includes asymmetrically isomerizing a specific compound in the presence of a ruthenium catalyst and a base, thereby giving an optically active citronellal, and selectively cyclizing the optically active citronellal in the presence of an aluminum catalyst. The aluminum catalyst is obtained by reacting a specific hydroxy compound and at least one aluminum compound selected from a specific alkylaluminum compound, a specific hydride aluminum compound, a specific linear aluminoxane and a specific cyclic aluminoxane.

Abstract: Disclosed herein is a method for producing an alcohol and an amine from an amide under an atmosphere of hydrogen with the use of, as a catalyst, a ruthenium complex that is easily prepared, easy to handle, and relatively cheaply obtained. Specifically, the method is a method for producing an alcohol and/or an amine from an amide compound under an atmosphere of hydrogen with the use of as a catalyst, a ruthenium carbonyl complex represented by the following general formula (1): RuXY(CO)(L) (1) wherein X and Y may be the same or different from each other and each represents an anionic ligand and L represents a tridentate aminodiphosphine ligand containing two phosphino groups and a —NH— group.

Abstract: Disclosed herein is a method for producing an alcohol and an amine from an amide under an atmosphere of hydrogen with the use of, as a catalyst, a ruthenium complex that is easily prepared, easy to handle, and relatively cheaply obtained. Specifically, the method is a method for producing an alcohol and/or an amine from an amide compound under an atmosphere of hydrogen with the use of as a catalyst, a ruthenium carbonyl complex represented by the following general formula (1): RuXY(CO)(L) (1) wherein X and Y may be the same or different from each other and each represents an anionic ligand and L represents a tridentate aminodiphosphine ligand containing two phosphino groups and a —NH— group.

Abstract: The present invention relates to a ruthenium carbonyl complex that is represented by the following Formula (1): RuXY(CO)(L)??(1) (in the Formula (1), X and Y, which may be the same or different from each other, represent an anionic ligand and L represents a tridentate aminodiphosphine ligand which has two phosphino groups and a —NH— group), its production method, and a method for production of alcohols by hydrogenation-reduction of ketones, esters, and lactones using the complex as a catalyst. The ruthenium carbonyl complex of the invention has a high catalytic activity and it can be easily prepared and handled.

Abstract: The present invention relates to a ruthenium carbonyl complex that is represented by the following Formula (1): RuXY(CO)(L)??(1) (in the Formula (1), X and Y, which may be the same or different from each other, represent an anionic ligand and L represents a tridentate aminodiphosphine ligand which has two phosphino groups and a —NH— group), its production method, and a method for production of alcohols by hydrogenation-reduction of ketones, esters, and lactones using the complex as a catalyst. The ruthenium carbonyl complex of the invention has a high catalytic activity and it can be easily prepared and handled.

Abstract: Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein R1 represents a spacer; R2, R3, R4, R5, R6 and R7 independently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R8, R9, R10, R11, R12 and R13 independently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.

Abstract: Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein R1 represents a spacer; R2, R3, R4, R5, R6 and R7 independently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R8, R9, R10, R11, R12 and R13 independently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.

Abstract: The present invention provides a method for producing optically active amines of formula (9) or (10): which comprises reacting an imine equivalent of formula (6): with an alkene of formula (7) or an alkyne of formula (8): in the presence of a chiral catalyst, which method does not require additional procedures such as introduction and removal of protecting groups and gives said amines with high purity and high operability. The optically active amines are useful as synthetic 15 intermediates for pharmaceuticals, agrochemicals, etc.

Abstract: This invention provides a novel process for producing optically active 3-hydroxy-&ggr;-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-&ggr;-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

Abstract: This invention provides a novel process for producing optically active 3-hydroxy-&ggr;-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle.

Abstract: Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.

Abstract: Disclosed is a process for the preparation of a 4-substituted azetidinone derivative, which comprises reacting an azetidinone derivative and an amide compound in the presence of a magnesium compound such as those represented by the following formulas (II): and (IV): represented by the following formula (III): MgR5R6  (III) wherein R5 represents a C1-12 alkyl group, a C2-5 alkenyl group, a 5- to 8-membered alicyclic group which may be substituted by a lower C1-4 alkyl group, a phenyl group which may be substituted by a lower C1-4 alkyl group, a lower C1-4 alkoxy group or a halogen atom or a benzyl group which may be substituted by a lower C1-4 alkyl group, a lower C1-4 alkoxy group or a halogen atom, and R6 represents a halogen atom, a methanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, a trifluoromethanesulfonyloxy group, an acetoxy group which may be substituted by a halogen atom or a cyano group or an OR7 group (R7 representing